66962-52-5

Usage

InChI:InChI=1/C6H11N3S2/c1-2-3-4-7-5-8-9-6(10)11-5/h2-4H2,1H3,(H,7,8)(H,9,10)

Upstream product

• 2209-28-1 1,6-dibutyl-2,5-dithiobiurea 
• 66870-06-2 1-butyl-2,5-dithiobiurea 
• 75-15-0 carbon disulfide 
• 6610-31-7 4-butyl-3-thiosemicarbazide 
• 592-82-5 butyl isothiocyanate 

Relevant academic research and scientific papers

CERTAIN NEW 4-(2-((5-(SUBSTITUTEDAMINO)-1,3,4-THIADIAZOLE-2-YL)THIO)ACETYL)BENZENESULPHONEAMIDE DERIVATIVES AND A METHOD FOR THE SYNTHESIS OF SAID DERIVATIVES

The invention relates to a certain new 4-(2-((5-(substitutedamino)-1,3,4-thiadiazole-2-yl)thio)acetyl)benzenesulphonamide derivatives for use in pharmaceutics, chemical and pharmaceutical industry, and to a method for the synthesis of said derivatives.

Synthesis of new benzothiazole derivatives bearing thiadiazole as monoamine oxidase inhibitors

Monoamine oxidases (MAO) are enzymes that catalyze the oxidative deamination of monoamines such as dopamine, noradrenaline, adrenaline, and serotonin. Recent studies have shown that numerous benzothiazole derivatives exhibit hMAO inhibitory activity in the micromolar concentration range. In this study, a novel series of benzothiazole-thiadiazole (5a-5l) was synthesized and characterized their chemical structures by 1H-NMR, 13C-NMR, and Mass spectroscopy. These compounds were evaluated as inhibitors for types A and B MAO enzymes. Compounds 5f and 5l were the most active derivatives in the series with an IC50 values of 0.107 ± 0.003 and 0.128 ± 0.004, respectively. Furthermore, cytotoxicity of compounds 5f and 5l were investigated and found as non-cytotoxic.

Synthesis and characterization of a new series of thiadiazole derivatives as potential anticancer agents

Cancer is one of the most common causes of death in the world. Despite the importance of combating cancer in healthcare systems and research centers, toxicity in normal tissues and the low efficiency of anticancer drugs are major problems in chemotherapy. Nowadays the aim of many medical research projects is to discover new safer and more effective anticancer agents. 1,3,4-Thiadiazole compounds are important fragments in medicinal chemistry because of their wide range of biological activities, including anticancer activities. The aim of this study was to determine the capacity of newly synthesized 1,3,4-thiadiazole compounds as chemotherapeutic agents. The structures of the obtained compounds were elucidated using 1H-NMR, 13C-NMR and mass spectrometry. Although the thiadiazole derivatives did not prove to be significantly cytotoxic to the tumour tissue cultures, compound 4i showed activity against the C6 rat brain cancer cell line (IC50 0.097 mM) at the tested concentrations.

Novel 1,3,4-thiadiazole compounds as potential MAO-A inhibitors-design, synthesis, biological evaluation and molecular modelling

Monoamine oxidases (MAOs) are important drug targets for the management of neurological disorders. Herein, a series of new 1,3,4-thiadiazole derivatives bearing various alkyl/arylamine moieties as MAO inhibitors were designed and synthesized. All of the compounds were more selective against hMAO-A than hMAO-B. The half maximal inhibitory concentration (IC50) values of most of the compounds were lower than that of the common drug moclobemide (IC50 = 4.664 μM) and compound 6b was proven to be the most active compound (IC50 = 0.060 μM). Moreover, it was seen that compound 6b showed a similar inhibition profile to that of clorgyline (IC50 = 0.048 μM). The inhibition profile was found to be reversible and competitive for compound 6b with MAO-A selectivity. Molecular modelling studies aided in the understanding of the interaction modes between compound 6b and MAO-A. Furthermore, this compound was predicted to have a good pharmacokinetic profile and high BBB penetration. Therefore, such compounds are of interest towards developing new MAO inhibitors.

Synthesis and optimization of thiadiazole derivatives as a novel class of substrate competitive c-Jun N-terminal kinase inhibitors

A series of thiadiazole derivatives has been designed as potential allosteric, substrate competitive inhibitors of the protein kinase JNK. We report on the synthesis, characterization and evaluation of a series of compounds that resulted in the identifica

Alkali catalyzed thermal cyclization of 1-substituted and 1,6-disubstituted 2,5-dithiobiureas: Formation of 1,2,4-triazolidine-3,5-dithiones and/or 1,3,4-thiadiazoline-5-thiones

Alkali catalyzed thermal cyclization of 1-alkyl and 1,6-dialkyl-2,5-dithiobiureas (I, R=alkyl, R'=H and R=R'=alkyl) results in the formation of 4-alkyl-1,2,4-triazolidine-3,5-dithiones (V) (alkyl=Me or Et) and 2-alkylamino-Δ2-1,3,4-thiadiazoline-5-thiones (VI) (alkyl=n-Pr or n-Bu).Under the same conditions, 1-alkyl-6-aryl-2,5-dithiobiureas (I, R=alkyl, R'=aryl) give 2-arylamino-Δ2-1,3,4-thiadiazoline-5-thiones (IX) (alkyl=Me, Et, n-Pr or n-Bu) and 4-alkyl-1,2,4-triazolidine-3,5-dithiones (V) also when the alkyl groups are Me or Et.

Process for the production of 2-amino-5-mercapto-1,3,4-thiadiazole

2-Amino-5-mercapto-1,3,4-thiadiazoles can be produced in very high yields from thiosemicarbazides and carbon disulfide in aqueous phase by working in the presence of the corresponding ammonium salt of bis-2,5-mercapto-1,3,4-thiadiazole at a temperature above 40° C. Preferably the process is carried out in the presence of the mother liquor from a previous reaction.